Lithium Chloride → 3-Benzyloxy-5-isobutylbenzoic acid methyl ester

HRID 1430995Notes

Reaction equation

HRID 1430995 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[C:6]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=1.[Cl-].[Li+].[Br-].[CH2:30]([Zn+])[CH:31]([CH3:33])[CH3:32]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([CH2:30][CH:31]([CH3:33])[CH3:32])[CH:7]=[C:6]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 18945283Methyl 3-benzyloxy-5-(trifluoromethanesulfonyloxy)benzoateHCID 178448254HCID 178448254, compound

Product 1

HCID 585288613-Benzyloxy-5-isobutylbenzoic acid methyl esterYield 68%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a microwave reaction vial was added 3-benzyloxy-5-trifluoromethanesulfonyloxybenzoic acid methyl ester (70 mg, 0.179 mmol), lithium chloride (23 mg, 0.537 mmol), Pd(PPh3)4 (10 mg, 0.009 mmol) and 3 ml of THF. Isobutylzinc bromide (0.5 M in THF) (0.537 mL, 0.269 mmol) was added and the vial sealed. After heating in microwave reactor at 130° for 5 min the reaction mixture was adsorbed onto silica gel and purified by silica gel chromatography using an ethyl acetate-hexane gradient to afford 36 mg (68%) of 3-benzyloxy-5-isobutylbenzoic acid methyl ester. 1H NMR (300 MHz, DMSO-d6) δ 0.850 (d, 6H, J=6 Hz), 1.78-1.92 (m, 1H), 3.84 (s, 3H), 5.16 (s, 2H), 7.11 (d, 1H, J=2 Hz), 7.33-7.48 (m, 7H).

Workup

  1. customTo a microwave reaction
  2. temperatureAfter heating in microwave reactor at 130° for 5 min the reaction mixture
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b2464f6e83ef43aa9b5d763b1e907120
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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